CA2412298A1 - Ligature chimique naturelle etendue - Google Patents
Ligature chimique naturelle etendue Download PDFInfo
- Publication number
- CA2412298A1 CA2412298A1 CA002412298A CA2412298A CA2412298A1 CA 2412298 A1 CA2412298 A1 CA 2412298A1 CA 002412298 A CA002412298 A CA 002412298A CA 2412298 A CA2412298 A CA 2412298A CA 2412298 A1 CA2412298 A1 CA 2412298A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- substituted
- peptide
- electron
- ligation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
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- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical group OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium;hydroxide;hydrate Chemical compound [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical compound [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 description 1
- 229960004635 mesna Drugs 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 125000006384 methylpyridyl group Chemical group 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- PEECTLLHENGOKU-UHFFFAOYSA-N n,n-dimethylpyridin-4-amine Chemical compound CN(C)C1=CC=NC=C1.CN(C)C1=CC=NC=C1 PEECTLLHENGOKU-UHFFFAOYSA-N 0.000 description 1
- WOOWBQQQJXZGIE-UHFFFAOYSA-N n-ethyl-n-propan-2-ylpropan-2-amine Chemical compound CCN(C(C)C)C(C)C.CCN(C(C)C)C(C)C WOOWBQQQJXZGIE-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 238000007344 nucleophilic reaction Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- RUVINXPYWBROJD-UHFFFAOYSA-N para-methoxyphenyl Natural products COC1=CC=C(C=CC)C=C1 RUVINXPYWBROJD-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 230000015843 photosynthesis, light reaction Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 108010077112 prolyl-proline Proteins 0.000 description 1
- 230000016434 protein splicing Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000006894 reductive elimination reaction Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003342 selenium Chemical class 0.000 description 1
- 229960002718 selenomethionine Drugs 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- XBXCNNQPRYLIDE-UHFFFAOYSA-N tert-butylcarbamic acid Chemical compound CC(C)(C)NC(O)=O XBXCNNQPRYLIDE-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 125000000430 tryptophan group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C2=C([H])C([H])=C([H])C([H])=C12 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 108010073969 valyllysine Proteins 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/107—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides
- C07K1/113—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides without change of the primary structure
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/795—Porphyrin- or corrin-ring-containing peptides
- C07K14/80—Cytochromes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06086—Dipeptides with the first amino acid being basic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
- C07K5/06147—Dipeptides with the first amino acid being heterocyclic and His-amino acid; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0812—Tripeptides with the first amino acid being neutral and aromatic or cycloaliphatic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Gastroenterology & Hepatology (AREA)
- Peptides Or Proteins (AREA)
Abstract
La présente invention concerne des procédés et des compositions qui permettent d'effectuer la ligature chimique de constituants tels qu'un premier constituant comprenant un carboxythioester et de préférence une fraction .alpha.-carboxythioester et un deuxième constituant alkyle ou aryle thiol à 2 ou 3 chaînes carbone, N-substitué et de préférence N.alpha.-substitué pour produire un produit de ligature ayant une liaison amide N-substituée au niveau du site de ligature. Les réactants selon l'invention sont chimiosélectifs et la fraction alkyle ou aryle thiol peut être éliminée du produit de ligature. L'élimination de l'alkyle ou de l'aryle thiol donne lieu à une liaison amide naturelle au niveau du site de ligature. Les procédés et les compositions selon l'invention sont particulièrement utiles pour la ligature de peptides et de polypeptides. Le système de ligature selon l'invention peut être appliqué à une grande diversité de molécules et peut donc être utilisé pour générer des peptides, des polypeptides et d'autres polymères contenant des acides aminés ayant une liaison amide naturelle au niveau du site de ligature.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23133900P | 2000-09-08 | 2000-09-08 | |
| US60/231,339 | 2000-09-08 | ||
| PCT/US2001/028172 WO2002020557A1 (fr) | 2000-09-08 | 2001-09-07 | Ligature chimique naturelle etendue |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2412298A1 true CA2412298A1 (fr) | 2002-03-14 |
Family
ID=22868813
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002412298A Abandoned CA2412298A1 (fr) | 2000-09-08 | 2001-09-07 | Ligature chimique naturelle etendue |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP1315738A4 (fr) |
| JP (2) | JP2004508383A (fr) |
| KR (1) | KR20030061785A (fr) |
| CN (1) | CN1452632A (fr) |
| AU (2) | AU2001288937B2 (fr) |
| BR (2) | BR0113623A (fr) |
| CA (1) | CA2412298A1 (fr) |
| ES (1) | ES2360203T3 (fr) |
| IL (1) | IL154015A0 (fr) |
| MX (1) | MXPA03001450A (fr) |
| WO (1) | WO2002020557A1 (fr) |
| ZA (3) | ZA200300314B (fr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7781488B2 (en) * | 2002-06-10 | 2010-08-24 | Amylin Pharmaceuticals, Inc. | Post-cleavage sulfur deprotection for convergent protein synthesis by chemical ligation |
| EP1616003A4 (fr) | 2002-12-30 | 2007-06-20 | Gryphon Therapeutics Inc | Composes thioesters et selenoesters hydrosolubles et leurs procedes de production et d'utilisation |
| US8076299B2 (en) | 2005-10-25 | 2011-12-13 | Riken | Method for producing peptide thioester |
| WO2011017837A1 (fr) * | 2009-08-12 | 2011-02-17 | Xuechen Li | Ligature chimique native sur les sites de la sérine et de la thréonine |
| FR2952058B1 (fr) * | 2009-10-29 | 2013-10-04 | Centre Nat Rech Scient | Procede de ligation native de polypeptides |
| CN115058426B (zh) * | 2022-05-16 | 2024-07-16 | 上海志药科技有限公司 | 一种特异性识别SARS-CoV-19的核酸分子探针及其筛选方法、检测产品和应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6184344B1 (en) * | 1995-05-04 | 2001-02-06 | The Scripps Research Institute | Synthesis of proteins by native chemical ligation |
| WO1998028434A1 (fr) * | 1996-12-24 | 1998-07-02 | The Scripps Research Institute | Ligature chimique generale |
| US6307018B1 (en) * | 1996-12-24 | 2001-10-23 | The Scripps Research Institute | General chemical ligation |
-
2001
- 2001-07-12 BR BR0113623-2A patent/BR0113623A/pt not_active IP Right Cessation
- 2001-07-12 ES ES01952657T patent/ES2360203T3/es not_active Expired - Lifetime
- 2001-07-12 BR BR0113579-1A patent/BR0113579A/pt not_active IP Right Cessation
- 2001-09-07 JP JP2002525177A patent/JP2004508383A/ja active Pending
- 2001-09-07 IL IL15401501A patent/IL154015A0/xx unknown
- 2001-09-07 KR KR10-2003-7002775A patent/KR20030061785A/ko not_active Ceased
- 2001-09-07 WO PCT/US2001/028172 patent/WO2002020557A1/fr not_active Ceased
- 2001-09-07 CN CN01815351A patent/CN1452632A/zh active Pending
- 2001-09-07 CA CA002412298A patent/CA2412298A1/fr not_active Abandoned
- 2001-09-07 AU AU2001288937A patent/AU2001288937B2/en not_active Ceased
- 2001-09-07 EP EP01968707A patent/EP1315738A4/fr not_active Withdrawn
- 2001-09-07 AU AU8893701A patent/AU8893701A/xx active Pending
- 2001-09-07 MX MXPA03001450A patent/MXPA03001450A/es unknown
-
2003
- 2003-01-13 ZA ZA200300314A patent/ZA200300314B/xx unknown
- 2003-01-13 ZA ZA200300315A patent/ZA200300315B/en unknown
- 2003-01-24 ZA ZA200300659A patent/ZA200300659B/en unknown
-
2008
- 2008-02-06 JP JP2008025907A patent/JP2008150393A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IL154015A0 (en) | 2003-07-31 |
| KR20030061785A (ko) | 2003-07-22 |
| ZA200300659B (en) | 2004-03-05 |
| MXPA03001450A (es) | 2004-12-13 |
| BR0113579A (pt) | 2003-06-17 |
| BR0113623A (pt) | 2004-06-22 |
| EP1315738A4 (fr) | 2006-06-07 |
| ZA200300315B (en) | 2004-02-04 |
| JP2004508383A (ja) | 2004-03-18 |
| AU2001288937B2 (en) | 2005-04-28 |
| EP1315738A1 (fr) | 2003-06-04 |
| JP2008150393A (ja) | 2008-07-03 |
| AU8893701A (en) | 2002-03-22 |
| ES2360203T3 (es) | 2011-06-01 |
| WO2002020557A1 (fr) | 2002-03-14 |
| ZA200300314B (en) | 2004-02-04 |
| CN1452632A (zh) | 2003-10-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued | ||
| FZDE | Discontinued |
Effective date: 20080908 |